Well, one time I was playing an orc barbarian berserker. Charisma total negative 7. Int score 4. Will save 0. Anyway, we were at this super fancy dinner with a King who we REALLY needed to get on our side. Problem was, while the other party members were making an effort to eat properly with all the right utensils (and failing a bit), I had picked up the soup bowl to pour the contents down my throat, picked the chicken up whole barehanded, and stuck the forks in my hair. The king got really angry and demanded an explanation, looking ready to clap us all in irons for the offense.

Me: You say I bad manners? You lie! I show you best orc manners! I pay you high compliment, wash hands before eating, and you insult orc culture! Granpa Greatclub not like hear insult to culture!

Greatclub was a local orc chieftain with, like, 500 followers, a rather serious threat, could probably walk over the kingdom's armies. Of no relation whatsoever to my character. I rolled a nat'20 to my bluff.

King: ...(convulsive swallow) A thousand pardons, my good fellow. I meant no offense. But of course, I really should learn more about other cultures.

The King - and thus, the rest of the court - proceeded to eat with their fingers while sticking the utensils in their hair, and mimicking every other eating action I took.

That... that was brilliant! LMFAO!!! XD

In the vein of some of GM's actions in this comic, but utterly unintentional.

We were playing in a modern urban low-fantasy setting and my character was a Drow pimp/assassin (practically speaking, Wiz14) with Cha3 and no ranks in any social skill but Intimidate. Because of the various stuff that went down, he ended up casting off of Con instead of Int and I twinked his Con out the butt. Thus, high Fort save.

Right near the end of the campaign, we needed to get the massive cannons off of a trio of guard towers to let an enemy fleet into port. We had a Hulking Hurler in our party, half-giant who proceeded to make the requisite stupidly-high Str checks to rip two of the cannons out and hurl them into the air. One comes down into the ocean.

The DM rolled for direction and distance for the other, then just kept making rolls for about a minute, refusing to tell us why. I, by the way, was trying to intimidate a stubborn guard into letting me in to see the Prince. I was making really horrible Intimidate rolls, when in the middle of it the DM told me to make a Fort save. I did so, easily, and my character didn't react at all when the cannon that was ripped out came crashing down, right-side-up, aimed at the doorway he was trying to get through, right next to him.

Said exchange went about like this:

Me: Last chance or I'll see how well a crossbow works on you and the rest of your friends.

Guard: You and what army?

(Cannon comes crashing down)

Me: (Bluff nat20) ... Who needs an army when the gods are on my side? All praise to Armok.

Guard: (cacks his pants and lets me in)

How exactly does one cack ones pants?

It means shit, he shit his pants, badly.

From Latin cacare (“to defecate”) (From Wiktionary)

Ah. I thought it was a typo of 'crap'. Turns out it was another word for it.

Uncouth and Ugly Alien Force User in a Star Wars campaign, at a fancy party, trying to cover for the rest of the party who is robbing the place, panics when the others and some guards come blasting out of the kitchens, he tells the Hutt Diplomat that the guards are assassins trying to kill her (yes, the Hutt was a female at the time), and he and his allies were there to protect her from them. He rolled a nat 20, and voila, she believes him and calls her own lackeys to help fight the actual guards of the palace. He then, like an idiot, lets it slip who holds the loan on their ship, hoping to capitalize on her good favor to help them get out of it, which he lucks into a 19 and a borderline success, so she says she'll put in a good word for them (it did shave 1000 credits off their initial debt, then added 7000 because of the collateral damage at the party, and the face of the group failing the bluff check with the Houk who they owed the loan to... plus... because of something the force user said, they now had been assigned to escort and protect the Hutt on her journey).

Oh, same campaign, the Pilot (who also had charisma as a dump stat) actually bluffed the Houk into believing a derelict ship they found was worth 10x its actual value, thinking they'd use it to pay off their debt. Problem came up that 1) they could only bluff their way into 25% of the sell price, with the Houk eating the cost of towing, repairs, and black market selling it, 2) The Houk towed it and wouldn't give them their cut minus their debt to him, until after the sale... 3) Just cause they made him believe it was worth 10x the value, doesn't mean he could sell it for that much. Sufficed to say, they never got the debt expunged and the profit... the irony, had they not bluffed, the derelict was worth enough that, 25% of the sell of it, would have covered their debt, and they'd still have gotten 3-10% of the sell price in net profit.

...okay.

First time back behind the dice in years and years - taking a vanilla dual-wield ranger. Our party gets hired to recover this 'eldritch tome'...which, after we get hold of it, realize is pretty dangerous goods. We're worried what our patron is going to do with it, but our more Lawful party members are bound to complete the assignment (then see about neutralizing the evil this book holds afterwards).

So on our travels back to the city where our patron is living, we end up embroiled in a side quest of dealing with a wererat that is terrorizing the village we stop at.

...and find out that the wererat is actually the MAYOR (unbeknownst to even himself). NATURALLY we kill instead of subdue (we had half our party incapacitated and would've been wiped out if we kept up with a 'trap it' plan)...and so the guard put us all under wraps for wandering out of the sewers with their mayor's corpse and admitting we killed him. :P

After a few days, a magistrate is dispatched to determine culpability, along with an 'investigator' (think Inquisitor Torquemada), and while my (yep, int and cha weak) tank is on the stand giving testimony, I let slip WHY we were travelling - getting a magical tome for a private individual...

...and then the Investigator gets VERY interested in this, and begins to subtly divert the whole proceedings to getting as much information about this evil source of power (uh-oh).

...so I tell a little fib; I explain that we're *on*our*way*to*GET*the*book*. Situational bonus to a relatively small lie, and my exact wording bent the truth as little as possible, but my penalties would make STILL make my attempt risky...

...and, for the first time since we'd started the campaign, I managed to roll a natural 20. :)

We'd paid a fine to get the Mayor resurrected and cured, and were then sent on our way...likely with someone hired by the Investigator to watch us as we went to get 'the book'.

In retrospect, it's a shame the campaign got put on indefinite hold just a few sessions after; would've been interesting to have a third faction show up while we were finishing our commission and/or dealing with a 'potential danger to public safety' (the paladin's rationalization for possibly having to gank our employer after the job was done ;) )

Not me, nor do I have a clue who it is (or if it's actually a real story), but this is the first thing that comes to mind when I think of bluff.

>Make a bear character in D&D 3.5
>DM laughs
>Make bear a rogue, put every point I can into disguise
>Prestige class as a spy to get more disguise
>DM says I can't speak english
>Max out bluff
>By growling and gesturing, I can fake speaking a language I don't speak (english)

>use money to hire a butler NPC
>Give him magical item to let him speak bear

"GROWWWWWL"
"An excellent suggestion, Mister Bearington. We really should ask the group to investigate the Black Marsh

>Over the course of the game, be knighted as Sir Bearington
>Queen holds a dinner in my honor.
>A guest becomes the first man to ever make a perception check that can beat my disguise
>Shouts out loud
"HEY, THAT GUY'S NOT A GUY, HE'S JUST A BEAR!"
>Man is escorted out of the castle while the guards apologise profusely for the indignity
"We're so sorry, Sir Bearington, very sorry for this man's behavior"
"ROAR" *shrug*

Puts on a disguise to look like human guys, but you're not a man you're a bear, Boo!

I was in a D6 star wars campaign as a bounty hunter. My friend Shawn was playing a retired Imperial Captain. Will had a Jawa Jedi.

We were in a bar when a fight broke out. Will started cutting people's legs off. I blasted away with my blaster. Shawn broke for the door, getting past an Imperial patrol responding to the trouble.

A second patrol arrives as I and Will manuevered for the door. Shawn bluffed the second patrol that the first patrol had gone crazy.

The first patrol shot at me, but hit members of the second patrol. So they started shooting at each other while we made our escape
CES

One of my group's longest standing jokes began when one of our players, the guy who M'lady'd his way through any in-character interaction, tried his hand at a bluff but the GM called for specifically what was said. We were trying to extract information and our would-be informant had been lying to us pretty obviously the whole time but wouldn't crack.

So he says: "I know that you know that we know that you know that we know you know what we want to know--"

We didn't make it farther than that into his interrogation attempt, or even his roll, because the table broke down into a half hour of laughter.

This was less about my character not seeming plausible as I had a decent bluff but due to a terrible roll earlier I believed and important holy symbol our group needed to deliver was the symbol of Barney the dinosaur, and then when the queen arrived with the rest of my group (who I was separated from at the time) I get upset with her calling it differently and roll a bluff check and got a 7 but then the DM rolled a 1 and had me convinced the queen she lived her whole life in the same town as the symbol of Barney the dinosaur.

This was less about my character not seeming plausible as I had a decent bluff but due to a terrible roll earlier I believed and important holy symbol our group needed to deliver was the symbol of Barney the dinosaur, and then when the queen arrived with the rest of my group (who I was separated from at the time) I get upset with her calling it differently and roll a bluff check and got a 7 but then the DM rolled a 1 and had me convinced the queen she lived her whole life in the same town as the symbol of Barney the dinosaur.